The purpose of this contribution is to analyze the spatial distribution of the place names referred to the Tuscan territory, to fortified structures and settlements, through the study of the place names recorded geodatabase RE.TO.RE. (Regional Toponymic Repertory) created by the Tuscany Region with the scientific contribution of the Universities of Pisa, Florence and Siena. The Tuscan toponyms has been the object of both a synchronic study within each of the cartographic sources that make up the geographical database, and a diachronic analysis between the temporal thresholds in which the archive is articulated. The database, extrapolated from cartographic supports, in fact covers a time span between the first decades of the nineteenth century (nineteenth century land registries) and the most recent information series produced in the regional context (Carta Tecnica Regionale). In the contribution, the place names related in various ways to different types of structures and fortified settlements, such as castle, fort, tower, fortress, has been analyzed both in relation to the distribution and spatial aspects, and in reference to their evolutionary dynamics (persistence, disappearance, transformation), with the aim of identifying possible relationships between the territory and the distribution in time and space of the different types of fortifications. From a methodological point of view, the study has been carried out, in addition to the traditional tools of the topomastic survey, especially taking advantage of the potential of spatial analysis functions typical of geographical information systems.